How INSURICA Clients Gain an Edge with OutSail

Payroll errors that hit the general ledger, open-enrollment portals that freeze at midnight, new hires juggling four log-ins on day one – when HR technology falters, the ripple effects reach every corner of the organization.

Yet most employers still rely on a patchwork of legacy systems chosen under deadline pressure. INSURICA’s new collaboration with OutSail changes that equation, giving clients a clear, proactive path to a sturdier tech foundation.

Why getting HR tech right is so hard

Vendors promise “seamless” and “intuitive,” but getting the right tech stack in place feels anything but. Feature lists blur together, demos highlight best-case scenarios, and pricing can vary by tens of thousands of dollars once implementation and add-ons appear. It is little wonder the buying process can feel daunting and companies will stay with ‘the devil we know.’

Even after a platform is live, hidden gaps emerge: payroll doesn’t sync with time clocks, performance reviews live in a silo, benefits deductions misfire when an employee crosses state lines. Each fix costs time, money and employee goodwill.

A new, proactive playbook

INSURICA believes technology should strengthen – not strain – your benefits and people strategy. By partnering with OutSail, our team can now offer an end-to-end HR tech advisory service at no extra cost to clients:

• Tech-stack audit: A short strategy call and intake survey produce a map of every system, integration and manual workaround in play.
• Tailored vendor shortlist: Within one to two business days, OutSail delivers side-by-side comparisons built on real pricing and performance data from more than 220 providers.
• Guided evaluations: Weighted scorecards, targeted demo agendas and expert questions keep the buying team focused on must-have capabilities rather than sales theatrics.
• Negotiation support: Line-by-line proposal reviews flag hidden fees, benchmark rates and spotlight flexible terms before you sign. In recent engagements employers have trimmed 10 to 20 percent from software costs.
• Implementation backup: Readiness checklists, skill-gap analysis and a vetted network of implementation partners help projects launch on time and on budget.

“In our role, we often hear a lot of feedback—usually frustration—about HRIS and payroll vendors,” said Lindsay Neal, INSURICA Senior Consultant. “By the time it reaches us, the client is already dealing with multiple issues. What we appreciate about OutSail is that it allows us to offer more than just secondhand feedback. Instead of relying solely on what we’ve heard from other clients, we can share objective, structured insight into which vendors are the best fit for a client’s specific needs.”

Real-world impact

Organizations that have followed this framework report measurable wins. Restaurant tech company Olo saved $300,000 and stood up a new enterprise HRIS in just 90 days, while consumer-goods manufacturer Dorel cut $1 million over three years by moving to a more integrated platform.

Beyond the balance sheet, employees notice smoother onboarding, faster PTO approvals and a single source of truth for their data—small moments that add up to stronger retention and brand reputation.

What this means for INSURICA clients

• Fewer surprises: You see every cost, integration gap and timeline risk before a contract is signed.
• More bandwidth: HR and finance leaders reclaim dozens of hours otherwise spent wrangling RFPs and demos.
• Lasting value: The same advisory team that helps you choose a system stays available for mid-cycle tune-ups and future expansions.

Take the first step

If your HR platforms feel more like a set of stopgaps than a strategic asset, let’s talk. Your INSURICA advisor can schedule a complimentary HR Tech Audit powered by OutSail and put you on the road to technology that works as hard as your people do.

For more Employee Benefits resources, contact INSURICA today.

This is not intended to be exhaustive nor should any discussion or opinions be construed as legal advice. Readers should contact legal counsel or an insurance professional for appropriate advice.